US4542165A
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Polyurethane based on epoxy-containing polymer polyol and process for making the same
Assignee: Sanyo Chemical Industries Ltd
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Filing: 1984-08-16
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Granted: 1985-09-17
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Expires: 2004-08-16
Abstract
Abstract Polyurethane resins having high rigidity and improved physical properties such as mechanical strengths and heat resistance are obtained by reacting a polyisocyanate with a polymer polyol derived from an epoxy-containing monomer, for example, glycidyl esters of unsaturated mono- and dicarboxylic acids, and a polyol, and bringing about ring-opening reaction of epoxy radicals in the presence of an epoxy curing agent, simultaneously with, or before or after the urethane-forming reaction.
Inventors
- 👤 Koji Kumata
- 👤 Masao Fukuda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 08:57
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/02; C08G59/04; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/63; C08G59/18; C08G59/40; Y; Y10; Y10S; Y10S521/00; Y10S521/902
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
110 words
A process for producing a cellular or noncellular polyurethane having improved rigidity and heat resistance, which comprises: reacting at least one organic polyisocyanate with a polyol component in the presence of or in the absence of a blowing agent, at least a part of the polyol component being at least one epoxy-containing polymer polyol derived from at least one polyol having an equivalent weight of 200-4,000 and at least one ethylenically unsaturated monomer comprising an epoxy radical-containing monomer; and bringing about ring-opening reaction of the epoxy radicals, in the presence of an epoxy curing agent with or without an epoxy curing accelerator, simultaneously with, before or after the urethane-forming reaction.
Claim 2
Dependent Claim
110 words
A process for producing a cellular or noncellular polyurethane having improved rigidity and heat resistance, which comprises: reacting at least one organic polyisocyanate with a polyol component in the presence of or in the absence of a blowing agent, at least a part of the polyol component being at least one epoxy-containing polymer polyol derived from at least one polyol having an equivalent weight of 200-4,000 and at least one ethylenically unsaturated monomer comprising an epoxy radical-containing monomer; and bringing about ring-opening reaction of the epoxy radicals, in the presence of an epoxy curing agent with or without an epoxy curing accelerator, simultaneously with, before or after the urethane-forming reaction.
Claim 3
Dependent Claim
28 words
The process of claim 1, wherein said curing agent is at least one compound selected from the class consisting of organic polyisocyanates, polyamines, acid anhydrides and Lewis acids.
Claim 4
Dependent Claim
44 words
The process of claim 1, wherein said polymer polyol is produced by polymerizing, in situ in said polyol, (a) at least one epoxy radical-containing monomer, and (b) acrylonitrile, methacrylonitrile or combination of them, with or without (c) one or more other ethylenically unsaturated comonomers.
Claim 5
Dependent Claim
47 words
The process of claim 1, wherein the epoxy radical-containing monomer is at least one compound selected from the class consisting of unsaturated hydrocarbon oxides, and unsaturated esters, ethers, urethanes, amides or acetals, which contain one or more epoxy radicals selected from 1,2-, 1,3-, 1,4- and 1.5-epoxide radicals.
Claim 6
Dependent Claim
32 words
The process of claim 1, wherein the epoxy radical-containing monomer is at least one monomer selected from the class consisting of unsaturated hydrocarbon oxides, glycidyl radical containing monomers and tetrahydrofuran ring-containing monomers.
Claim 7
Dependent Claim
44 words
The process of claim 5, wherein the glycidyl radical containing monomer is selected from the class consisting of glycidyl esters of unsaturated monocarboxylic acids, diglycidyl esters of unsaturated dicarboxylic acids, mono-C 1 -C 18 alkyl-monoglycidyl esters of unsaturated dicarboxylic acids, and unsaturated glycidyl ethers.
Claim 8
Dependent Claim
19 words
The process of claim 5, wherein the glycidyl radical-containing monomer is glycidyl methacrylate, glycidyl acrylate, or combination of them.
Claim 9
Dependent Claim
13 words
The process of claim 5, wherein the glycidyl radical-containing monomer is glycidyl methacrylate.
Claim 10
Dependent Claim
45 words
The process of claim 3, wherein said comonomer (c) is at least one monomer selected from the class consisting of unsaturated hydrocarbons, substituted styrenes, acrylic and substituted acrylic monomers, vinyl esters, vinyl ethers, vinyl ketones, other substituted vinyl monomers, unsaturated dicarboxylic acids and esters thereof.
Claim 11
Dependent Claim
17 words
The process of claim 3, wherein said comonomer (c) is methyl methacrylate, styrene or combination of them.
Claim 12
Dependent Claim
20 words
The process of claim 1, wherein at least 3% by weight of said unsaturated monomer is the epoxy radical-containing monomer.
Claim 13
Dependent Claim
30 words
The process of claim 3, wherein said polymer polyol is produced from 5-95% of (a), 5-95% of (b) and 0-60% of (c), based on the total weight of the monomers.
Claim 14
Dependent Claim
33 words
The process of claim 1, wherein said polyol having an equivalent weight of 200-4,000 is at least one selected from the class consisting of polyether polyols, polyester polyols, urethane polyols and vinyl-modified polyols.
Claim 15
Dependent Claim
19 words
The process of claim 1, wherein said polymer polyol contains 30-70% by weight of polymer derived from said monomer.
Claim 16
Dependent Claim
46 words
The process of claim 1, wherein the ring-opening reaction is brought about in the presence of at least one epoxy curing accelerator, selected from the class consisting of amines, basic alkali metal compounds, metal halides, organo metal compounds, quaternary ammonium compounds, phosphorus compounds and borate esters.
Claim 17
Dependent Claim
50 words
The process of claim 1, wherein said polyisocyanate is reacted with said polyol component in the presence of at least one catalyst for NCO reaction, selected from the class consisting of tertiary amines, secondary amines, alkali metal compounds, phosphines, metal chelate compounds, organo tin compounds, and other organo metal compounds.
Claim 18
Dependent Claim
37 words
The process of claim 1, wherein said polyisocyanate is reacted in the presence of at least one blowing agent, selected from the class consisting of halogenated hydrocarbons, low-boiling hydrocarbons, halogen-free volatile organic solvents and reactive blowing agents.
Claim 19
Dependent Claim
39 words
The process of claim 1, wherein the polyurethane is produced in the presence of at least one additive, selected from the class consisting of epoxy resins, surfactants, flame retardants, retardants, colorants, internal mold release agents, stabilizers, germicides and fillers.
Claim 20
Dependent Claim
79 words
The process of claim 1, wherein the polyol component comprises at least 20% by weight of said polymer polyol, and 0-80% by weight of at least one other active hydrogen atom-containing compound selected from the class consisting of high molecular weight polyols having an equivalent weight of 200-4,000, high molecular weight polyamines having an equivalent weight of 200-4,000, and low molecular weight compounds containing at least two active hydrogen atom-containing groups and having an equivalent weight less than 200.
Claim 21
Dependent Claim
28 words
The process of claim 1, wherein said curing agent is used in an amount of 0.5-200 parts by weight per 100 parts by weight of said polymer polyol.
Claim 22
Dependent Claim
32 words
The process of claim 1, wherein a Lewis acid is used as said curing agent in an amount of 0.5-20 parts by weight per 100 parts by weight of said polymer polyol.
Claim 23
Dependent Claim
39 words
The process of claim 1, wherein a polyamine or acid anhydride is used as said curing agent in such an amount providing an equivalent ratio of (NCO group+epoxy radical)/(active hydrogen atom-containing group+reactive group of said curing agent) of 0.7-1.3/1.
Claim 24
Dependent Claim
32 words
The process of claim 1, wherein an organic polyisocyanate is used as said curing agent in such an amount providing an equivalent ratio of NCO group/(active hydrogen atom-containing group+epoxy radical) of 0.3-1.3/1.
Claim 25
Dependent Claim
14 words
The process of claim 1, wherein NCO index in the urethane-forming reaction is 80-120.
Claim 26
Dependent Claim
21 words
The process of claim 1, wherein NCO index in the urethane-forming reaction is 300-1,000 to produce isocyanurate rings in the polyurethane.
Claim 27
Dependent Claim
35 words
The process of claim 1, wherein the ring opening reaction is brought about to crosslink between polymer portions of said polymer polyol or between polymer portion of said polymer polyol and polyurethane segment, or both.
Claim 28
Dependent Claim
53 words
The process of claim 1 wherein said polyisocyanate is reacted with said polyol component by conditioning them to a temperature of 25°-90° C., intimately mixing said components under a pressure of 100-200 kg/cm 2 g, injecting said mixture into a mold preheated to a temperature 30°-120° C., and thereafter demolding the resulting article.
Claim 29
Dependent Claim
12 words
A cellular or noncellular polyurethane, obtained by the process of claim 1.
Claim 30
Dependent Claim
13 words
The polyurethane of claim 28, having a density of 0.01-1.4 g/cm 3 .
Claim 31
Dependent Claim
11 words
A polyurethane molded article, obtained by the process of claim 27.
Claim 32
Dependent Claim
10 words
A crosslinked polyurethane, obtained by the process of claim 26.
Claim 33
Dependent Claim
20 words
The process of claim 1, wherein said ring-opening reaction of epoxy radicals is brought about simultaneously with the urethane-forming reaction.
Claim 34
Dependent Claim
19 words
The process of claim 1, wherein the ring-opening reaction of epoxy radicals is brought about after the urethane-forming reaction.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-09-16 | 1989-03-18 | 1989-09-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-16 | 1993-03-18 | 1993-09-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-16 | 1997-03-18 | 1997-09-17 | $7700.00 | Window Closed / Lapsed |